Tanshinone I

Base Information

• Chemical Name: Tanshinone I
• CAS No.: 568-73-0
• Molecular Formula: C18H12O3
• Molecular Weight: 276.291
• Hs Code.: 29329990
• UNII: 03UUH3J385
• DSSTox Substance ID: DTXSID90972247
• Nikkaji Number: J12.294G
• Wikidata: Q27247588
• Metabolomics Workbench ID: 132984
• ChEMBL ID: CHEMBL363535
• Mol file: 568-73-0.mol

Synonyms:tanshinone;tanshinone I;tanshinone II A;tanshinone II B;tanshinone IIA;tanshinone IIB;TTE-50

Chemical Property of Tanshinone I

Chemical Property:

• Melting Point: 233-234 °C
• Boiling Point: 498 °C at 760 mmHg
• Flash Point: 245.9 °C
• PSA: 47.28000
• Density: 1.324 g/cm³
• LogP: 4.09560
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble1mg/mL
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 276.078644241
• Heavy Atom Count: 21
• Complexity: 471

Purity/Quality:

more than 96% ^*data from raw suppliers

Tanshinone I ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC3=C(C2=CC=C1)C(=O)C(=O)C4=C3OC=C4C
• Recent ClinicalTrials: Tanshinone in Polycystic Ovary Syndrome
• Uses: Tanshinone I is an extract from Danshen (Radix Salvia miltiorrhizae) and has been used for the treatment of cerebrovascular diseases such as ischemic stroke.

Technology Process of Tanshinone I

There total 31 articles about Tanshinone I which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(-)-dihydrotanshinone I (20958-19-4,87205-99-0) → Tanshinone I (568-73-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 36h; Ambient temperature;

DOI:10.1016/S0040-4039(00)91882-3

Reference yield: 65.0%

1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione (77769-21-2) → Tanshinone I (568-73-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene; at 110 ℃; for 24h;

DOI:10.1039/c8ob00567b

Reference yield: 45.0%

3-hydroxy-8-methylphenanthrene-1,4-dione (30684-15-2) + chloroacetone (78-95-5) → Tanshinone I (568-73-0)

Guidance literature:

With ethanol; ammonium acetate; acetic acid; In toluene; for 2h; Reflux; Darkness;

DOI:10.1021/acs.jnatprod.7b00238

upstream raw materials:

(-)-dihydrotanshinone I

1-(5-methyl-[1]naphthyl)-ethanone

2-Diazo-1-(5-methyl-naphthalen-1-yl)-ethanone

(+)-danshexinkun A

Refernces

• 1、 Foulkes, Matthew J.,Tolliday, Faith H.,Henry, Katherine M.,Renshaw, Stephen A.,Jones, Simon. "Evaluation of the anti-inflammatory effects of synthesised tanshinone I and isotanshinone I analogues in zebrafish". . . Retrieved 2020/10/20.
• 2、 Wu, Nan,Ma, Wei-Cong,Mao, Sheng-Jun,Wu, Yong,Jin, Hui. "Total Synthesis of Tanshinone i". . p. 1697 - 1700. Retrieved 2017/05/31.